NP-MRD: Showing NP-Card for 3-(3,4,5-trimethoxyphenyl)propanoic acid (NP0292089)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 23:27:15 UTC

Updated at

2022-09-09 23:27:15 UTC

NP-MRD ID

NP0292089

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(3,4,5-trimethoxyphenyl)propanoic acid

Description

3-(3,4,5-Trimethoxyphenyl)propanoic acid, also known as 3,4,5-trimethoxydihydrocinnamic acid, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-(3,4,5-Trimethoxyphenyl)propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-(3,4,5-Trimethoxyphenyl)propanoic acid has been detected, but not quantified in, herbs and spices. This could make 3-(3,4,5-trimethoxyphenyl)propanoic acid a potential biomarker for the consumption of these foods. 3-(3,4,5-trimethoxyphenyl)propanoic acid is found in Piper crassinervium, Piper longum and Piper retrofractum. A monocarboxylic acid consisting of propionic acid having a 3,4,5-trimethoxyphenyl substituent at the 3-position.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    1.1307   -3.2669   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8166   -2.0774   -1.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -1.0668   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1461   -1.1827   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7624   -0.1525    0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1875   -0.2999    0.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0210    0.2371   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4450    0.1095   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7614   -0.3910    1.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4641    0.5219   -0.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    0.9890    0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671    1.0838    0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9476    2.2529    0.6368 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3295    3.3187    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9204    0.0772   -0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2546    0.1714   -0.7476 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -0.2783    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0353   -3.8608   -0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1606   -3.0119   -2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124   -3.8776   -2.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7028   -2.0777   -0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4152   -1.4026    0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.2406    1.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7394    1.3033   -0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7768   -0.2773   -1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6839    1.5146   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5141    1.8203    1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667    4.1426    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464    3.0209    2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4515    3.6642    0.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0264   -0.8961   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8126   -0.9191    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7595    0.5710    0.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 15  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END


  Mrv0541 02241217292D          

 17 17  0  0  0  0            999 V2000
   -0.7122   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7122   -1.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7123   -1.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7123   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286   -1.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    2.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.6799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    2.6799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -1.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -2.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -1.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
  7 15  1  0  0  0  0
  8 11  1  0  0  0  0
  9 17  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292089

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCC(O)=O)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h6-7H,4-5H2,1-3H3,(H,13,14)

> <INCHI_KEY>
ZCYXGVJUZBKJAI-UHFFFAOYSA-N

> <FORMULA>
C12H16O5

> <MOLECULAR_WEIGHT>
240.2524

> <EXACT_MASS>
240.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.783292530784554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4,5-trimethoxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.582548973333333

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.868942411211532

> <JCHEM_PKA_STRONGEST_BASIC>
-4.445857816580141

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
61.3562

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,4,5-trimethoxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.329  -0.382   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.329  -1.922   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -2.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.330  -1.922   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.330  -0.382   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.382   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -2.692   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   1.922   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -2.692   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000  -4.232   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334   2.692   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   4.232   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   5.002   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   5.002   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.999  -1.920   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.335  -5.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.999  -1.920   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    2   15                                                       
CONECT    8    6   11                                                       
CONECT    9    4   17                                                       
CONECT   10    3   16                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    7                                                            
CONECT   16   10                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trimethoxyphenylpropionic acid	ChEBI
3-(3',4',5'-Trimethoxyphenyl)propionic acid	ChEBI
beta-(3,4,5-Trimethoxy phenyl)propionic acid	ChEBI
3,4,5-Trimethoxyphenylpropionate	Generator
3-(3',4',5'-Trimethoxyphenyl)propionate	Generator
b-(3,4,5-Trimethoxy phenyl)propionate	Generator
b-(3,4,5-Trimethoxy phenyl)propionic acid	Generator
beta-(3,4,5-Trimethoxy phenyl)propionate	Generator
Β-(3,4,5-trimethoxy phenyl)propionate	Generator
Β-(3,4,5-trimethoxy phenyl)propionic acid	Generator
3-(3,4,5-Trimethoxyphenyl)propanoate	Generator
3,4,5-Trimethoxy-benzenepropanoic acid	HMDB
3,4,5-Trimethoxydihydrocinnamic acid	HMDB
3,4,5-Trimethoxyhydrocinnamic acid	HMDB
3-(3,4,5-Trimethoxyphenyl)propionic acid	HMDB
beta -(3,4,5-Trimethoxy phenyl)propionic acid	HMDB
3-(3,4,5-Trimethoxyphenyl)propanoic acid	ChEBI
3,4,5-Trimethoxydihydrocinnamate	Generator

Chemical Formula

C₁₂H₁₆O₅

Average Mass

240.2524 Da

Monoisotopic Mass

240.09977 Da

IUPAC Name

3-(3,4,5-trimethoxyphenyl)propanoic acid

Traditional Name

3-(3,4,5-trimethoxyphenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(CCC(O)=O)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C12H16O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h6-7H,4-5H2,1-3H3,(H,13,14)

InChI Key

ZCYXGVJUZBKJAI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Piper crassinervium	LOTUS Database	35616633
Piper longum	LOTUS Database	35616633
Piper retrofractum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:583580 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.75	ALOGPS
logP	1.58	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.36 m³·mol⁻¹	ChemAxon
Polarizability	24.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030254

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002078

KNApSAcK ID

Not Available

Chemspider ID

58390

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

64860

PDB ID

Not Available

ChEBI ID

583580

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(3,4,5-trimethoxyphenyl)propanoic acid (NP0292089)

MOL for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)

3D MOL for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)

3D SDF for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)

3D-SDF for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)

PDB for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)

3D PDB for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)

SMILES for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)

INCHI for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)

Structure for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)

3D Structure for NP0292089 (3-(3,4,5-trimethoxyphenyl)propanoic acid)